Iodoethane → 1-Bromo-3-(4-ethoxybenzyl)-4-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-bromo-2-fluoro-benzyl)-phenol (6.0 g, 21.0 mmol) in anhydrous N,N-dimethylformamide (20 mL) cooled at 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.02 g, 25.6 mmol). After stirring at 0° C. for 45 minutes, iodoethane (2.08 mL, 25.6 mmol) was added dropwise and the resulting mixture was allowed to warm up to room temperature. After 18 hours, the reaction mixture was quenched with water and extracted twice with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 10% ethyl acetate in heptane to afford 4.6 g (58% yield) of the desired product as a yellow oil.

Provenance & Evidence